Azo-coloring-matter.



l particularlysuitable shades, and which are also particularly suit- STATES PATENT onrion.

ERNST FUSSENEGGER, OF. EUDWIGSHAFEN-ON-THELRH1NE,.GERMANY,

ASSIGNOR TO BADISOHE ANILIN & SODA FABRIK, OF LUDWIGSE .HAFEN-QN-THE-RHINE, GERMANY, A CORPORATION OF BADEN.

' AjZQC OLOR lN G-MATTER.

Specification of Letters Patent.

Patented Nov. 28, 1905.

Application filed August 4, 1905. Serial No. 272,787.

To all whom it may concern.-

doctor of philosophy and chemist, asubject of the Emperor of Austria-Hungary, residing at Ludwigshafen-omthe-Rhine, in the Kingdom of Bavaria, German Empire, have invented new and useful Improvements in Azo Coloring- Mattersmf which the following is a specification.

My intientionriates to the manufacture and production'of azo coloring-matters which are for use in the form of their lakes.

In the specification of German Patent No. 117,167 is described the production of 1.3-dihydroxy-quinolin, and lhave now discovered that by the action of diazo compounds'of the benzene or naphthalene series on this 1.3.-di-

hydroxy-quinolin new azo coloring-matters can be obtained which can be used for dyeing wool, producing from yellow to orange-red able for the preparation of lakes whose shades are also within the range of from, yellow to orange-red. The color of the dyes so obtained ranges from a lemon-yellow to orangered, and those dyes which are obtained from amins which contain no sulfo group and from amins which contain no carboxyl group are insoluble in water, while those dyes which are obtained from an amin-sulfo-acid or from ah amin-carboxylic acid can be converted into diificultly soluble or insoluble lakes, according to the well-known methods of preparing such lakes.

My newcoloring-matters on being reduced with tin andhydrochloric acid give rise to amido-dihydroxy quinolin, which has the power of reducing ammoniacal-silver solution in the cold and which in the form of its bydrochloric-acid salt crytallizes fromalcohol in fine colorless needles.

The following examples illustrate how some of the new coloring-matters can be obtained according to my invention, which, however, is

not confined to these examples. The parts 'amido-dihydroxy-quinolin.

water, to which also sufficient sodium carbon ate has been added to maintain the whole alkaline, stir for half an hour, (30 minutes,) filter olf the yellow coloring matter, wash with water, and grind to a homogeneous paste.

Example 2: Diazotize three hundred and seventeen (317) parts of crystallized sodium naphthionate in the usual manner and allow the solution to run at ordinary temperature into asolution of two hundred 'and five (205) parts ofthe disodium salt of 1.3-dihydroxyquinolin, to which also sufiicient sodium carbonate has been added to maintain the whole then warm to a temperature of from fifty to sixty degrees centigrade, (50 -60 (1,) filter off the coloring-matter, wash with a dilute solution of common salt, press, and dry.

alkaline, stir for half an hour, (30 minutes,)

Example 3: Diazotize two hundred and' of the disodium salt of 1.3-dihydroxy-quinolin, to which also suflicient sodium carbonate has been added to maintain the whole alk'aline, stir for from three to four (3-4) hours at ordinary temperature, filter off the coloringmatter, wash with a dilute solution of common salt, press, and dry.

, Example 4: Diazotize three hundred and fifty-seven (357) parts of amidoazo-benzenedisu'lfo-acid in the 'usual manner and'allow' the solution to run, at ordinary temperature into a solution of two hundred and five (205) parts of the disodium salt of 1.3dihydroxyquinolin, to which also sufiicient sodium carbonate has been added to maintain the whole alkaline, stir for half an hour, (30 minutes,)

then'warm to'a temperature of from fifty to sixty degrees-'centigrade, (50 -60 filter ofi the coloring-matter, wash with a dilute solution of common salt, press, and dry.

Now what I claim is:-

1. As new articles of manufacture the azo coloring matters which can be obtained by combining a d'iazo compound with 1.3-dihydroxy-quinolin, which dye unmordanted wool from yellow to orange-red shades, which in the form of theirlakes possess from yellow to orange-red shades and which upon reduc tion with tin and hydrochloric acid yield 2. As a new article of manufacture the azo coloring-matter which can be obtained by combining diazotized sulfanilic acid with 1.3- dihydroxy-quinolin, which dyes unmordanted wool yellow shades, which in the form of its lakes possesses yellow shades and which upon reduction with tin and hydrochloric acid yields sulfanilic acid andamido-dihydroxy-quinolin.

In testimony whereof I have hereunto set my hand in the presence of two subscribing IO Witnesses.

ERNST FUSSENEGGER.

Witnesses:

J. ALEC. LLOYD, Jos. H. LEUTE. 

